ArticleJournal of the American Society for Mass Spectrometry2013
Study of the gas-phase intramolecular aryltrifluoromethylation of phenyl(trifluoromethyl)iodonium by ESI-MS/MS.
Article in Journal of the American Society for Mass Spectrometry, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.
What it found
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
2 citing papers in PubMed.
- Intramolecular Halogen Transfer via Halonium Ion Intermediates in the Gas Phase.Journal of the American Society for Mass Spectrometry · 2016Article
- Mass spectrometric study of the gas-phase difluorocarbene expulsion of polyfluorophenyl cations via F-atom migration.Journal of the American Society for Mass Spectrometry · 2013Article
Corrections and comments
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Authors and funding
4 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The gas-phase reactions of the reactive λ(3)-phenyl(trifluoromethyl)iodonium (PhI(+)(III)CF3, 1 at m/z 273) to the radical cation of iodobenzene (PhI(•+), 2 at m/z 204) via the loss of ·CF3 and the radical cation of trifluoromethylbenzene (PhCF3(•+), 3 at m/z 146) via the loss of ·I, were studied by electrospray ionization tandem mass spectrometry (ESI-MS/MS). Interestingly, the gas-phase intramolecular coupling reaction of CF3 with phenyl via the CF3 migration process of 1 at m/z 273 from iodine to the phenyl to give 3 at m/z 146 could only occur according to an intramolecular aromatic substitution mechanism. Density functional theory (DFT) calculations showed that the gas-phase intramolecular aryltrifluoromethylation of 1 at m/z 273 to 3 at m/z 146 occurred via a Meisenheimer complex intermediate (MC), where the triplevalent I center of 1 was reduced to monovalent I. Most importantly, the structure of 3 at m/z 146 derived from 1 at m/z 273 in ESI-MS/MS process was confirmed by comparison of its MS/MS with that of an authentic PhCF3(•+) at m/z 146 acquired from the electron ionization (EI)-MS/MS analysis of PhCF3. Thus, our studies revealed the intrinsic reactivity tendencies of λ(3)-phenyl(trifluoromethyl)iodonium under solvent-free conditions.
Identifiers
23479313What OpenQuestion holds
Registered trials
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